Sodium hydride → HCID 21455225, compound

HRID 1606449Notes

Reaction equation

HRID 1606449 reaction equation
[H-].[Na+].Cl.[CH3:4][N:5]([CH2:7][CH2:8]Cl)[CH3:6].[CH2:10]([N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][C:15](=[O:23])[C:14]2=[CH:24][S:25][CH:26]=[C:13]12)[CH3:11]>CN(C)C=O>[CH3:4][N:5]([CH3:6])[CH2:7][CH2:8][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:12]([CH2:10][CH3:11])[C:13]2=[CH:26][S:25][CH:24]=[C:14]2[C:15]1=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 12521647HCID 12521647, compound

Product 1

HCID 21455225HCID 21455225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.31 g. of 55% sodium hydride-mineral oil dispersion and 0.50 g. of dimethylaminoethylchloride hydrochloride in 25 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.43 g. of 4,9-dihydro-4-ethyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one and stirring is continued for 18 hours. The reaction mixture is cooled, quenched with water, and extracted with chloroform. The dried chloroform extracts are concentrated to an oil, which is purified by preparative thin layer chromatography on silica gel with 10:1 benzene-methanol as eluent. The oily solid thus obtained is recrystallized from hexane to give white crystals, m.p. 75°-77°C.

Workup

  1. additionA mixture of 0.31 g
  2. additionTo the mixture is added 0.43 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. extractionextracted with chloroform
  6. concentrationThe dried chloroform extracts are concentrated to an oil, which
  7. customis purified by preparative thin layer chromatography on silica gel with 10:1 benzene-methanol as eluent
  8. customThe oily solid thus obtained
  9. customis recrystallized from hexane
  10. customto give white crystals, m.p. 75°-77°C.

Sources & evidence

ORD record
ord-0e9d03a370a3472ea387556c0d582fe8
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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